JARED REMY HAD GLIDED THROUGH his first five criminal cases, but prosecutors thought the sixth one would be different.

Compared to what he had been charged with in the past — beating and choking his ex-girlfriend while she held their baby, cracking a friend over the head with a beer bottle in a jealous fit, elbowing and cursing out a police officer — the case that landed in Lowell District Court in January 2001 seemed minor: Threatening to commit a crime.

But for the first time, prosecutors had a victim willing to testify against Remy, son of one of the most beloved figures in New England.

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He was 22 and could not keep a job or stay out of trouble. His parents had hired him the same high-priced lawyer who had prevailed over the district court prosecutors in Jared’s prior cases. So far that lawyer was five for five, sparing Remy jail time, a guilty finding, or anything more than temporary probation.

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But prosecutor Joshua E. Friedman did not see Jerry Remy’s son as a young man with a record clean of convictions, charged now with a minor offense. He saw him as steroidal and entitled, violent and unrepentant. Tiffany Guyette, his alleged victim, saw him that way, too. She said Remy had been abusing her since she got pregnant by him at 15, four years earlier.

Since then, Guyette said, he had tried to push her from a moving car while she was pregnant, waited for her in the dark with a baseball bat, and repeatedly paged her with the number 187, street slang for murder.

For all that, however, she had not spoken against him in court before, believing his promises that he would change, she said.

Then a counselor told her she needed to stand up to break the cycle of abuse. So when Remy allegedly unleashed another death threat over the phone, Guyette notified police. She resolved to face him in court.

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She wrote a letter to the judge, describing her “roller coaster” experience and warning that Remy was growing more brazen. She did not know if he could be redeemed, but held out hope that the right message — his first “guilty” finding, time behind bars, and meaningful counseling — could restore the “sweet and caring Jared” she once knew.

Prosecutor Friedman agreed, wanting a “short, sharp sentence to hopefully teach him some kind of lesson that this was not OK.”

The judge set trial for June. But Guyette never got the chance to testify. When they reconvened, Judge Neil J. Walker accepted a proposal from defense lawyer Peter Bella. Over the prosecutor’s objections, Walker continued and then dismissed the case.

Thirteen years, 14 more cases, and one murder count against Remy later, Guyette’s letter remains on file in Lowell, its last line hauntingly prescient. “If he does not learn to handle his anger,” she warned, “he could ultimately hurt me, my son, someone else, or himself.”

JARED REMY WAS THE KING of second chances. A review of hundreds of pages of court files and police records revealed accounts that he terrorized five different girlfriends starting when he was 17, and that courts repeatedly let him off with little more than probation and his promise to stay out of trouble. He rarely did.

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Now 35, Remy has been arrested or brought to court as the defendant in 20 different criminal cases, mostly for charges of violence against, or intimidation of, women, including his pending case for allegedly murdering his girlfriend, Jennifer Martel, in Waltham last August.

‘If he does not learn to handle his anger, he could ultimately hurt me, my son, someone else, or himself.’

Remy has been found guilty just twice, and both times his lawyer persuaded a judge to let him walk with a suspended sentence, defying the wishes of prosecutors.

Often he benefited from victims who did not want to testify, whether from fear or forgiveness, leading prosecutors to drop the case. But even when cases seemed airtight, judges often rewarded Remy with a nearly free pass — temporary probation without the stain of a guilty finding. Most offenders are lucky to get two such reprieves. He got six.

And on more than 10 occasions while already serving probation or waiting for an earlier case to be resolved, Remy was arrested again on new charges or otherwise ran afoul of the law — a pattern of incorrigibility that would ordinarily get a person locked up.

But he continued to walk, with judges extending his probation or finding creative solutions to help him avoid jail, like ordering him to move home with his parents and observe a curfew — a measure common in juvenile courts, but rarely employed for adults.

Bella, Jared Remy’s longtime defense attorney, said he does not believe Remy “got any special treatment” in court.

“What happened to his cases happened because of the facts of those cases and the circumstances of those cases, and not because he was Jared Remy,” Bella said.

Still, Bella said that Remy benefited because victims wavered — and acknowledged that as a former prosecutor with decades of experience he knew the ins and outs of the system, helping Remy fare better than he might have with a public defender or the less experienced counsel he could have afforded without his parents’ support.

“This is an old story for the American judicial system. You get a high-priced attorney, you get better justice,” said Friedman, the former Lowell prosecutor. “If he had been Jared Smith from a well-off family, he may have gotten the same result.”

But he was not Jared Smith. He was the son of the man recognized as the president of Red Sox Nation, Jerry Remy — the home-grown infielder-turned-broadcaster and air-guitar-playing commercial pitchman, best-selling author, and restaurant impresario revered as “The RemDawg.”

The Remys declined to be interviewed but issued a statement through one of the family’s lawyers. In it, Jerry Remy acknowledged Jared’s “significant number of criminal charges” as well as his history of “anger and lack of self-control” issues into his 20s.

Jennifer Martel Memorial Fund

At age 27, Jennifer Martel was coming into her own, with a job promotion, plan to become a teacher, and caring for her daughter, Arianna.

“I can also say that, unfortunately, no parents are immune from trouble with their children. My wife and I did everything we could to provide Jared with the necessary professional help,” Jerry Remy said, indicating that they thought Jared’s problems had been brought under control, noting a stretch from December 2005 to last summer without an arrest for violence. “What occurred in August 2013 took my family by complete surprise. We loved Jennifer and treated her as if she was our own daughter.”

The Remys did not address the seemingly endless reservoir of financial support that Jared enjoyed over the years for his mounting legal bills or for rent, cars, car insurance, gym memberships, tanning, cable TV, and other expenses, which several people described, including Guyette and Kristina Hill, a neighbor and close friend of Martel’s.

Jared’s brother and sister, like Jared, were represented by Bella in court appearances for their own handful of encounters with the law. Some were for lesser matters like marijuana possession and disturbing the peace. But each also has been arrested in recent years on more serious charges. Jordan Remy admitted in a 2010 case that there was enough evidence to convict him of following home and groping a woman who rebuffed him at a bar. Jenna Remy admitted sufficient evidence for a conviction in court this month on charges she broke into an ex-boyfriend’s home and assaulted the police officers who tried to arrest her. Like Jared, both got probation while avoiding convictions.

But Jared Remy’s trouble defined him in a way his siblings’ did not. Interviews with more than 40 former friends, neighbors, co-workers, police officers, and others contacted by the Globe — including many speaking publicly for the first time — paint a picture of a disturbed, havoc-wreaking life and a criminal justice system that failed to rein it in.

Even as a young man, he had several encounters with police, and three witnesses now say Remy at 18 was an instigator behind an unprovoked and brutal beating of a former schoolmate that left the teen with a severe brain injury. “He’s just toxic,” said Candice Wright, who participated in the beating and said she has carried the weight of regret for 17 years. “He preyed on certain people.”

Last August, after Jared Remy allegedly assaulted Martel, slamming her against a bathroom mirror, Martel spent the night at Hill’s apartment next door. Hill said she encouraged Martel to go to court the next morning to extend an emergency restraining order against Remy. But Martel told her that she had promised the Remys she would stay home, Hill said. In his statement, Jerry Remy said the family did not discourage Martel in any way from extending the restraining order. Whatever the reason, Martel did not go to court, and Jared was released. Prosecutors later acknowledged they put too much stock in Martel’s absence. The next night, she was dead.

Jared Remy pleaded not guilty to murder and assault and is being held without bail while awaiting trial. The murder left the couple’s now 5-year-old daughter, Arianna, without a mother, upended the lives of those who cared about Martel, and sent shock waves throughout New England. Until then, Jared Remy’s pattern of aggression was known only in a fairly small circle. Just one of his many arrests — for a 2005 domestic assault — had made news before.

A little over three years after that arrest, Remy’s father seemed hopeful that Jared’s worst days were behind him. “It’s an episode that’s in the past,” Jerry Remy told the Globe in early 2009, referring to the arrest that had made the news. “He’s now the proud father of two children. But it’s something he really regrets.”

AT FIRST GLANCE, Jared Remy and his siblings glowed — three beautiful children, the boys often in matching polos or Red Sox tees. But by the mid-1980s, some Weston neighbors were wary of Jared and his reputation for throwing rocks.

From an early age, Remy wrestled with dyslexia and aggression, and by adolescence, the Weston Public Schools paid for him to attend the alternative Gifford School, a nurturing center for children from around the region with learning or emotional challenges.

Jared Remy, shown in his 1994-95 yearbook.

Initially, Remy was allowed to continue playing after-school sports at Weston High. The 1993-94 yearbook shows him as a handsome, baby-faced 15-year-old on the freshman basketball team — nothing like the muscle-bound hulk too big to fit in back of a police cruiser on the night of his murder arrest two decades later.

But by the school year of 1995-96, Remy’s behavioral problems cost him the privilege of playing sports at Weston High, and even his place at Gifford, forcing him to study at home with a private tutor, Guyette and other classmates said. But he continued to date a girl at Weston High, and their breakup that winter — documented in police reports — triggered a possessive anger he would exhibit for years.

Joanne Rathe/Globe Staff

For a time, Remy attended the Gifford School in Weston.

On Jan. 25, 1996, Jerry Remy called Weston police worried that his now 17-year-old son was still harassing the girl, that Jared had made some troubling phone calls and shoved her at least once. Police reports show the ex-girlfriend and her father considered getting a restraining order but worried it might make Jared retaliate. Jerry Remy asked police to help his son “understand the seriousness of his actions,” according to a Weston police report.

“Jared indicated that although he didn’t want [a restraining order] issued against him, it wouldn’t be a big deal if one was,” the officer who spoke with them wrote in the report. “He also didn’t think it was a big deal if he got arrested. Jared had a very bad attitude and acted disrespectful towards his father.”

Meanwhile, Jared Remy had been calling the girl’s new boyfriend to torment him, too, the 15-year-old boyfriend told Weston police, saying he had started taking the phone off the hook to avoid upsetting his mother. The boy’s father had died, and Jared threatened to make him “join his father in the grave” if he did not stop dating Jared’s ex-girlfriend, police wrote, based on the boy’s account.

In February, the same week Jerry left for spring training that year, Jared showed up at Weston High and had a charged encounter with the new boyfriend, according to a police report, which said three girls claimed Jared vowed to return with a gun and shoot the boy. Then he raced off, reportedly making obscene gestures to others on the road, police wrote. At the Remy house, police sat down with Jared, his mother Phoebe Remy, and John O’Rourke, Jerry’s best friend and future business partner. O’Rourke, they wrote, offered to bring the boys together to “talk this out.” No charges followed.

Jared was soon booked for Florida, apparently to join his father at spring training. But before leaving, he called his ex-girlfriend and her friend to warn them to prepare for “a war” when he returned, according to police reports.

Tiffany Guyette, shown in a 1996-97 yearbook photo, said Remy abused her while they dated and while she was pregnant with their son.

But there is no record of trouble when Jared got back, and he turned his attention that spring to a new girlfriend from Gifford — 14-year-old Tiffany Guyette. “We fell hard for each other,” she said in an interview.

Guyette — who has changed her name to distance herself from her past, asked that only her birth name be used — was drawn to Jared’s clean-cut looks and troublemaker’s edge.

For Guyette, who had spent time in a foster home, the rides in Phoebe Remy’s Lexus were thrilling. So were the gifts that she said followed: a diamond bracelet, a pager with service.

She and Jared spent a lot of time alone, and in January 1997 Guyette, then 15, discovered she was pregnant.

THAT MONTH, 18-year-old Jared Remy drove a group of their friends to a house party in Franklin. Drinking in a basement crowded mostly with strangers, Remy seethed at the sight of a familiar face: John Lloyd, a 15-year-old Gifford student whom Guyette had known for years, according to Guyette and two others who accompanied them, Candice Wright and Selina Elliott.

John Lloyd, whom Remy allegedly helped beat up at a party in Franklin.

Chubby and eager to be liked, Lloyd was a friend, not a threat to her relationship with Remy, Guyette said. But Remy was jealous.

Wright, who described herself as powerfully built at 16 but also an anxious girl, was drinking Captain Morgan rum from the bottle. Remy flattered her about her reputation for standing up for friends and tried to goad her into ambushing Lloyd with Remy’s 40-ounce Haffenreffer bottle, Wright and the other witnesses said.

As their small group headed outside to leave the party, Wright hit Lloyd on the back of the head. The bottle shattered. The boy crumpled. Remy cheered and led a charge of teens in kicking Lloyd repeatedly while he was down, Guyette and Elliott said. Then they piled into Remy’s Volvo wagon and drove off.

Franklin police found Lloyd that night — Jan. 18, 1997 — incoherent and sprawled down a set of stairs. They sent him to a local hospital, but he was soon airlifted to UMass Medical Center with “life-threatening head injuries,” according to the police report.

Lloyd survived, but his cognitive function and mood seemed permanently altered, his relatives said. He spiraled through seven dark years before dying at 22 of a gunshot wound ruled a suicide.

Wright told police about her role — resulting in a probation sentence — but not Remy’s. She wanted to accept blame and protect her friends, she said. When authorities interviewed Guyette, she also kept quiet about Remy’s part. He had persuaded her, she said, to lie on his behalf.

“I was a minor, I was pregnant, and I was petrified,” Guyette said.

THE REMY HOME in 1997 was a roomy clapboard-sided Colonial with a pool, set back from a leafy Weston street. Jerry Remy by then was a fixture on the Red Sox broadcasts but not yet a one-man industry. For Guyette, it was a new world and, though she had some misgivings, it seemed in ways to be an idyll.

Often at odds with her own mother, she frequently stayed with the Remys, and Phoebe drove the 15-year-old to her doctor appointments. As Guyette grew bigger, a change came over Jared, she said; he belittled her weight gain and became verbally abusive.

One night that spring, he erupted while driving, flooring the accelerator, whipping his car around Weston, and trying to undo Guyette’s seat belt and shove her out the door, she said.

Guyette said she escaped at a railroad crossing and ran to the Remy home, where she told Phoebe what had happened and wanted to report the incident to police. She said Phoebe offered to let her take refuge in a basement bedroom, and neither contacted authorities.

Suzanne Kreiter/Globe staff

Selina Elliott accompanied Tiffany Guyette, Jared Remy, and Candice Wright to a party in Franklin in 1997. At the party, Remy, who was 18 at the time, allegedly led a group of teens in kicking John Lloyd after Wright hit him with a bottle, Guyette and Elliott say.

Selina Elliott — who says she witnessed John Lloyd’s beating, and whose older brother was Jared Remy’s friend from Gifford — often hung out with the couple. She remembered Remy could be sweet and generous, driving them around and springing for movie tickets for the group. But she said she also saw him burst into rage, one night beating Guyette so badly that Guyette thought she would miscarry.

In September 1997, Guyette delivered a healthy son at Newton-Wellesley Hospital.

After transferring to a school better suited for teen mothers, Guyette developed what she called a “crush on a new boy” and tried breaking up with Remy. But the baby bound them together, and he would have no part of a split. Remy sometimes tracked her to the boyfriend’s Lowell home, she said, lurking in the dark with a bat or a knife.

BY SUMMER 1998, Jared Remy — 5-foot-7 and barely 140 pounds — openly discussed taking steroids and bought them with an allowance he dubbed his “lifting money,” Guyette said. She said she feared interacting with him, and when they spoke by phone Aug. 6 to arrange the handoff of a car seat for their son, she asked to meet in a public place. He insisted she come to his parents’ house, according to the Weston police report that followed.

As soon as Guyette arrived, she and Jared started arguing, the report said. He erupted, hitting and choking her while she held their baby, and then snapping the wipers, smashing the windshield, bashing the side, and shattering the lights of her car, according to the police report.

“I observed all of the marks on her as well as black smudged finger and hand prints around her neck,” an officer wrote in the report. Phoebe Remy witnessed the fight and told police Guyette had hit back, the report said. But police charged only Jared, arresting him
on charges of domestic assault and malicious destruction of property.

The next day, 19-year-old Jared was arraigned in Waltham District Court for the first time, released with an order not to abuse or contact Guyette. But within weeks he had called her, asking to meet secretly at the Natick Mall, in violation of the order, Guyette said.

He told her he still loved her and promised to change, she said. Guyette bought it.

“This sounds like a soap opera now,” she said. But “I was extremely naive and didn’t see that it was actually a way to break the restraining order, to continue the cycle of abuse.”

Back in court on Oct. 21, 1998, Bella, the defense attorney, set the template that they would use down the long line of future cases: Remy would waive his right to a jury trial and hope for leniency from a judge. He would admit sufficient facts — acknowledging enough evidence for a jury conviction, stopping short of a full admission or apology — but ask to be let go without incarceration or a guilty finding.

Prosecutors objected, court records show. Guyette said she spoke on Remy’s behalf. And Judge Gregory C. Flynn rewarded him with the next best thing to outright dismissal, a “continuance without a finding” — a judgment known in Massachusetts criminal courts as a CWOF (pronounced “quaff”), probation without a conviction.

It was an official second chance. Jared was ordered to attend counseling, check in regularly, and stay trouble-free for one year — or return to court and risk having the CWOF replaced with stricter punishment.

He almost made it. Just two weeks before his probation was to end, Remy got so upset after learning Guyette was spending time with one of his old Gifford friends, Erik Jackiewicz, that he drove to Jackiewicz’s Norwood apartment on Oct. 9, 1999, and smashed him on the head with a beer bottle, according to Guyette, Jackiewicz, and court records.

But instead of a cascade of consequences, Remy received another CWOF and probation, this time in Dedham District Court.

THAT WINTER OF 2000, Jared Remy seemed to go off the rails. Now 21, he floated between his childhood home and an apartment on Waltham’s Moody Street, where he shared a seemingly stormy living arrangement with a new girlfriend from Billerica, 20-year-old Lysa Gianacopolis, and a former Gifford classmate, Andrew Ufland.

On Feb. 23, 2000, Gianacopolis moved out suddenly at 4 a.m. — leaving under the watchful eye of Waltham police, who came at the request of a friend helping her move to prevent a “breach of peace,” according to their report.

Ufland soon moved out, too, and on March 25 he showed up at the Waltham station requesting a restraining order against Remy. He said Jared had barged into the Ford dealership where Ufland worked, threatening to kill Ufland and blaming him for his latest breakup. Ufland also claimed Remy boasted about having a gun, though Ufland had never seen it, police wrote.

Ufland decided not to complete the request for a restraining order, the report said, but he asked police to tell Remy to leave him alone. He also informed them they could find steroids in Remy’s closet. At the apartment, officers searching with Remy’s consent found a gym bag in his closet. When they opened it, “several hunting knives” tumbled out, along with a baggie holding nine uncapped syringes, though no drugs, police wrote.

A week later, Jared Remy himself called police at 2 a.m. from an address on Spring Street in Waltham, asking for help with an unwanted person, according to a police report. Officers arrived to find him standing in the street, “yelling and screaming” at his mother through the window of her silver BMW, the report said. A man not identified in the report got out and explained they had taken Jared home after a disagreement with a girlfriend and “just wanted to make sure everything was OK” before leaving.

As a crowd of gawkers grew, Jared Remy continued to scream and became even more “belligerent,” a police report said. When an officer approached to ask a question, Remy “gave me a slight elbow to the stomach area and told me to f--- off,” the officer said in the report. Cuffed and arrested for creating a disturbance, Remy apologized from the back of the cruiser but said he was furious that “his mother was butting into his life.”

Gianacopolis, meanwhile, contacted police in Lowell to say Remy had repeatedly called her there that weekend, declaring his love and vowing to “kill her if they don’t get back together,” according to a police report. She told police he was a drug user and that he had warned her to “watch her car.”

Gianacopolis, who declined to be interviewed for this story, told police she was unwilling to testify. “All she wants is to be left alone,” according to police, who filed a criminal complaint against Remy April 4 for making threats. With Gianacopolis absent from court the next month, Peter Bella argued that the charge was flimsy and the woman had “no imminent fear” of Remy. He got the case knocked down to a magistrate’s hearing, and there is no indication in the file the hearing was ever held — merely rescheduled four times before the charge was dismissed.

A photo of the Remy family — Jerry (from left), Jared, Jordan, Phoebe, and Jenna — was included on a congratulations page for Jenna in her 2003 yearbook from Weston High School. The photograph was taken around 1999.

OUTSIDE OF JERRY REMY’S statement describing his son’s anger and self-control problems, little in the public record gives insight on Jared Remy’s emotional state or psychological issues. But a therapist’s letter filed in connection with a court case in 2001 provides a rare, if fleeting, glimpse. Psychologist Harry M. Leichtman wrote that Remy had an anxiety disorder and that “in difficult moments, Mr. Remy’s neurological/biochemical state works against him.” Remy was prescribed medications to help control his condition, but the therapist expressed frustration that Remy refused to take them out of fear that would mark him as “damaged good[s].”

The letter, which Bella submitted around the time of a February 2001 probation violation hearing, claimed regular therapy had helped Remy control his “impulsivity, distractibility [and] overly aggressive responses,” to distinguish between sad and mad feelings, and express himself properly.

Still, the therapist did not say Remy’s condition was an excuse for his behavior. “Like the rest of us,” Leichtman wrote, “Mr. Remy must be held responsible for his actions.”

Remy’s emotions apparently again got the better of him when he called Guyette on Jan. 21, 2001, asking permission to take his son to a birthday party for the child of a new girlfriend.

At that point, Guyette, 19, had sole custody of the child after winning a two-year court battle initiated by Jerry and Phoebe Remy in which a guardian appointed by the court to investigate the child’s welfare, Bette Winik, ultimately sided with Guyette. “Bette was the one that really laid out that Jared was not doing what the court asked, that his parents were enabling him, and that Tiffany was the better parent,” said Maxa Berid, a family lawyer who represented Guyette. (Guyette lost custody in 2007, after the Remys prevailed in a second case, brought at a time Guyette was in another abusive relationship.)

But under the 2000 court order granting Guyette custody, Jared Remy was not allowed to take the child out alone, and on the phone, Guyette refused Remy’s request, according to an affidavit Guyette filed Jan. 22, the day after Jared’s call. He erupted, hurling a string of expletives and threatening “to kill me and my [n-word] boyfriend,” Guyette wrote, requesting a restraining order. Police in Lowell, where Guyette had an apartment, charged Remy with making threats.

A trial was set for June 1, 2001. This time, Guyette was prepared to testify, and prosecutor Joshua Friedman thought Remy would finally get convicted and sentenced. Jail time for a charge of making threats was rare, but given Remy’s lack of remorse and pattern of behavior, Friedman asked for three months in the House of Correction, with three more months suspended.

The case was Remy’s sixth in 27 months, and he would pick up a seventh that spring after a fight with an acquaintance in a Waltham tow yard. Lowell District Court Presiding Justice Neil Walker acknowledged that probation alone did not seem to be working with Remy.

“It’s at this point [incumbent] upon me to find a way to get through [to] Mr. Remy and impose something even more of an incentive to him,” Walker said, according to a court transcript.

But even after Remy in court acknowledged threatening Guyette, the judge did not impose jail or even convict him. He accepted Bella’s proposal to continue Remy’s case without formal judgment — not even a CWOF — and dismiss it altogether if Remy behaved and remained in counseling. The prosecutor objected.

A judiciary spokeswoman this month said Walker and other judges could not comment on any case involving Remy.

More than 12 years later, Walker’s dismissal in Lowell still galls Friedman. “It was so wrong what they did, as a matter of law,” he said, in phone and e-mail interviews from Tajikistan, where he works on human rights issues. “The justice system of the commonwealth let [Guyette] down.”

SEEMINGLY UNCHASTENED, Remy dived into a new relationship, this time with a 21-year-old Waltham mother named Ryan McMahon, that police and court records depict as achingly similar to the relationships that came before. On at least eight occasions, police reported McMahon’s claims of Remy’s harassment, threats, and physical abuse. In restraining-order affidavits, she alleged Remy was using cocaine, painkillers, marijuana, and alcohol in addition to steroids.

Though McMahon spoke to police immediately after their fights about her fear of him, and of the injuries she said he inflicted on her, she would go back to him and elect to not testify as the cases wound through court, making prosecution difficult, according to court records.

Early in the relationship, Remy lived with a group of friends in a rented house at 15 Rich St. in Waltham. Some of the roommates had lengthy records. In one six-month period starting in late 2002, police responded to calls involving the apartment 16 times.

Andrew Ufland, the former Gifford classmate who had tipped police off to the needles in Jared’s gym bag, had apparently made up with Remy by that time and moved into the basement, though he would come to realize it was a mistake.

Ufland, in December 2002, asked police for a restraining order and an escort to retrieve his belongings. In an affidavit, he said he’d tried to move out four days earlier, but Remy attacked Ufland and his father and threatened, “I’m going to kill you, you [slur for Jewish people],” before another roommate intervened. Ufland died last year; his father confirmed the incident but declined to comment further.

Remy would eventually move from Rich Street, too, though not by choice. In March 2003, he would be charged with striking one of McMahon’s closest girlfriends in the head with a bottle at a bar. And on July 3, McMahon told police that Remy had called over the preceding week and threatened several times to kill her. She said he then accosted her at work at the Tanning Hut in Waltham and followed her outside, where he allegedly punched her in the back.

Arrested on a warrant the next day, July 4, Remy quickly posted bail. He got as far as the street before taking out his phone and calling McMahon again to berate and threaten her, police said, bringing more charges.

Noting the string of cases, Judge Flynn of Waltham at an arraignment that Monday, July 7, allowed Remy to avoid jail but ordered him to move home with his parents and observe a 6 p.m. to 6 a.m. curfew while awaiting trial.

Phoebe Remy posted the $500 bail, court records show.

IN SEPTEMBER 2003, Remy was still living at home by court order as he turned 25. By then, he was an imposing figure. Years of steroids and intense weight-lifting workouts had helped him pack on 50 pounds of muscle, pushing him near 200 pounds, according to police reports and affidavits. He was bigger, louder, and more erratic than ever — and he seemed to behave with an air of invincibility, according to police and court records.

Right outside of Waltham District Court one morning that month — after hearings on three cases at once — he shouted into his cellphone with such volume as he was leaving that a police officer decided to run a quick records check. He discovered that Remy had a suspended license and pulled him over. When police towed Remy’s car, they found needles and steroids in his backpack and charged him with illegal possession of both as well as operating with a suspended license.

After one fight with McMahon the next summer, in July 2004, she told police that he had boasted to her “that he always wins,” according to a Waltham police report.

Though she said Remy had cut up her clothing and pictures and punched her in the face with a cordless phone, a Waltham judge again let him out on bail — Phoebe posted the $500 — this time with the agreement of prosecutors, who insisted that Remy try to find and keep a job.

He soon materialized as a security guard at Fenway Park, three other guards recalled. Instead of assigning him to crowd control at games, the Red Sox placed Remy on quiet day shifts, signing for packages and checking bags of fans touring the ballpark.

By the time the Red Sox won the 2004 World Series, Remy had amassed 15 criminal cases and at least nine speeding tickets and five accidents, according to state Registry of Motor Vehicles records. Still, that February, he was assigned to escort the new World Series trophy to the Berkshires for an appearance. He got pulled over doing 92 on the Pike, according to RMV records.

In November 2005, he dragged McMahon down stairs and beat her so badly he broke her nose, bloodied her lip, and left a welt around one eye, Waltham police wrote in a report that noted Remy fled to his parents’ house. Arrested there, he admitted to officers, “I slapped her around” — but dismissed the likely consequences as just “another year of probation,” according to the police report.

Though he said he made only $10 an hour at Fenway, he quickly produced the $3,000 bail to free himself that night. In court in Waltham for his arraignment the next morning, he ignored a restraining order and strode over to McMahon, according to a police report, and accused her of cheating. She forced him to examine her black-and-blue face. “Remy put his head down and said it was the Anedrol [Anadrol, a steroid],” police wrote in the report. According to the report, Remy told McMahon “that he was going to miss her . . . and said sorry.”

For the first time, prosecutors argued successfully for Remy to be locked up while awaiting trial. Judge Flynn deemed it necessary for McMahon’s safety.

Just six days later, McMahon returned to court, asking to lift the restraining order. “I am not in fear of . . . Jared Remy,” she wrote. Bella cited that request and asked that Remy be released to resume living with McMahon, provided they pursue couples counseling and Remy work on anger management. The judge said no.

After 81 days in the Middlesex Jail, Remy waived his right to trial and offered to plead guilty.

Prosecutors wanted at least a year of incarceration, followed by a long probation and completion of the state’s 40-week batterers program. Bella wanted Remy to be let out on probation. The judge agreed with Bella, releasing him and ordering him to complete the program and to stay drug and alcohol free.

In jail, being Jerry’s son made him a hero, Guyette recalled Remy boasting. “He’d brag about giving away his dad’s autograph” for favors, she said. “Having a full canteen, getting guys to shave his back.”

When he got out in January 2006, Remy’s Fenway job would be waiting for him. And it would lead him to the woman he is accused of killing.

JARED REMY MET JENNIFER MARTEL at a barbecue, when she was casually dating another Fenway security guard. It was 2007, about a year and a half after Remy had gotten out of jail. Short, dark-haired, and striking, Martel looked more than a little like a young Tiffany Guyette. And, like Guyette, the 22-year-old had also not had the easiest home life.

Growing up in Taunton, Martel had been 17 when her parents decided to follow her brother to Virginia for work, said Alexis Kirker, a younger cousin who grew up partly in the same household. Given a choice between dropping out of school and going with them or staying and fending for herself senior year, Martel stayed — working to pay for a tiny apartment and becoming the first in her family to finish high school, Kirker said.

Martel’s relationship with Remy started as a fling, Kirker and Hill, Martel’s friend and neighbor, said she told them. But she got pregnant unexpectedly, and she and Jared moved in together in Waltham’s Windsor Village.

Like others who knew Martel in Taunton, Kirker remembered the young woman as buoyant and self-assured. But when Kirker occasionally visited the new couple, she saw a different, more tentative side of her cousin. Kirker said Remy was cruel to Martel as she grew larger during pregnancy, “cutting her down about her weight — ‘you’re fat, you’re gross.’ ” Kirker and Hill said he belittled Martel’s family and felt that he drove a wedge between Martel and most of her relatives. Martel’s immediate family declined to speak with the Globe, citing an ongoing custody case involving Arianna.

As he was about to become a father for the second time, Jared Remy got snared in 2008 in a Major League Baseball steroid investigation that would cost him his job. Aggrieved, he spoke at length at the time with the Globe Spotlight Team.

Jared Remy shown with his mother, Phoebe Remy; father, Jerry Remy; daughter, Arianna; and Jennifer Martel in a Christmas 2012 photo that Martel had posted to her Facebook account.

Remy insisted he had no financial need to sell drugs and had never even discussed steroids with Red Sox players. But he defended his own use of illegal steroids, boasting of benching 475 pounds while calling the drugs safer than cigarettes and secondhand smoke.

“If I’m killing anyone,” Remy told a Globe reporter in a comment unpublished at the time, “it’s myself.”

Still, he seemed to be settling down, giving up hard drinking and spending time with his daughter, Arianna, though that often appeared to mean sitting with the child before a blaring big-screen TV while Martel was at work, several neighbors said.

To Windsor Village residents who regularly socialized in the courtyard — Remy often watching alone from the patio while Martel and Arianna joined in — he seemed more sad than terrifying. Without work, he rarely left the complex except to lift weights and tan, and sometimes to take his daughter to preschool, they said. Otherwise he stayed home watching TV or roaming the grounds with his dogs, walking them in the mornings with a sleep mask propped on his forehead.

Often, to run into him was to hear him bad-mouth others, spout off about college football and criminal law, and name-drop his father, all without taking a breath. “Getting Jareded,” neighbors called it.

By 27, Martel had come into her own — getting promoted to management at the Burlington Market Basket, losing weight, finishing an online associate’s degree, and getting accepted at Framingham State, a step toward her goal of becoming a teacher.

Jennifer Martel posted a photo of her and Jared Remy at Fenway on Facebook in 2010. They met while she was dating another Fenway guard.

She spent her days working, studying, seeing friends, and especially doting on Arianna — taking her to Crane Beach, Southwick’s Zoo, and the Children’s Museum, teaching her to eat apple slices before chicken nuggets.

“Jen wanted to raise Arianna to be socially respectful and to be a hard worker, to be all about self-improvement, to be responsible and kind,” Kristina Hill said.

As Martel flourished, neighbors said, Remy grew more irritable.

Hill heard frequent shouting through their shared apartment wall and said Remy made her nervous. Last June, as Hill, Martel, and their children gathered on the patio, the women expressed support for same-sex marriage, and Remy cut them off. Hill said he blurted out that he wanted “to get some guns and f--- up some queers.”

“Jen turned to him and was like, ‘This is why I’m going to leave you, because you say things like this.’ And then he went off on her,” said Hill, recalling Remy screaming and cursing — though Martel eventually calmed him down.

Jennifer Martel posted this photo of Jared Remy on Facebook in June 2009 with the caption “Mr dad.” The couple’s daughter, Arianna, was 9 months old at the time."

Still, Martel felt genuinely close to Jenna and Phoebe Remy, and she was tied to them financially, unable to provide the same life for Arianna on her own, Hill said. Just eight weeks before Martel’s death, the Remys helped her get her first new car; she proudly posted a picture of the odometer, registering 4.1 miles, on Facebook.

On Aug. 13, a Tuesday night, Martel, as she often did, went over to Hill’s with Arianna. The pattern of visits incensed Remy, who yelled at her to come back and called her on the phone, according to a police report and an affidavit Martel filled out seeking an emergency restraining order. Martel left the girl with Hill and went home to try to calm him, but Remy argued with her, grabbed her by the neck and slammed her head against a bathroom mirror, the report and Martel’s affidavit said.

Martel freed herself and fled next door to Hill’s, according to the report and affidavit. Remy followed behind and banged on the door. Unable to get in, he retrieved a spare key, unlocked the door and continued to scream at Martel. “I feared for my safety and called the cops,” Martel wrote in her affidavit.

Police were already on the way, apparently alerted by others who saw or heard the commotion. They arrested Remy on a charge of assault and battery with a dangerous weapon. At the station, he paid a $40 fee to release himself on personal recognizance, according to court records. Hill said Martel spent the night with her, and Remy stayed at his parents’. It had been eight years since his last assault charge.

Hill said she encouraged Martel to go to court in the morning to extend the order, but Martel told her she no longer planned to go, after communicating with the Remys. “She showed me a text message that said they had taken the key [to their apartment] away from Jared,” Hill said.

But Jared Remy returned. On the night of Aug. 15, according to police, prosecutors, and witnesses, Remy somehow got into the apartment and stabbed Martel in an attack that left a trail of blood throughout their home and ended on the patio, where he swung the knife at another neighbor, Ben Ray, who tried to intervene, and continued to savage Martel over Hill’s screams.

Hill called 911, then phoned her husband in Australia, where he had just arrived on business.

“Jen is dead!” she wailed. “Jen is dead!”

WHEN THE NEWS REACHED THEM, they all thought the same thing. Selina Elliott and Candice Wright, Joshua Friedman and Tiffany Guyette had seen it coming. “I was shocked, but I wasn’t surprised,” said Guyette, more than a decade after she wrote her cautionary letter to the court about Jared Remy.

“It’s a hard thing to say, that it’s just a matter of time, when anybody dies,” she said. “But no matter how many years he hadn’t been in trouble, I didn’t think he had changed.”

Friedman, the former prosecutor, read the headlines half a world away in Tajikistan. “It broke my heart,” he said. “You hate to say, ‘If only we had done something different.’ . . . We knew this guy was a bad apple.”

Yoon S. Byun/Globe Staff

Kristina Hill, shown in October, says she saw her friend, Jennifer Martel, stabbed to death on the patio next to her apartment in Waltham’s Windsor Village.

Half a year later, Kristina Hill has moved far from the apartment complex where she witnessed her friend’s murder. Still, she struggles to sleep.

Martel’s family spent an anguished Christmas without her. They doted on Arianna, who counted off the numbers that her mother had taught her before picking up a photo album and climbing into Alexis Kirker’s lap. Arianna pointed at the faces she saw in the pictures and narrated for her mother’s cousin. “Mommy. Me,” Kirker recalled the girl saying. “Mommy. Me.”

“I told her, ‘She’s looking over you, and she loves you, and you can talk to her whenever you want. She’s listening.’ ”

And in Waltham, a retired police sergeant named Walter Nelson thought back with sadness to the midsummer afternoon when he ran into Remy while they were letting their dogs run at Waverly Oaks park.

As Weston’s court officer, Nelson had signed the very first criminal complaint against 19-year-old Jared Remy and seen him arraigned many times over the years. But on that day, Remy regaled Nelson with talk of his love for Martel, and pride over his daughter. Remy said he had finally gotten his life in order, and for an hour, the two laughed and talked on a park bench. Nelson left with a smile on his face.